This article documents the innovative practices and initial outcomes from the Grand Rapids Engaged Department Initiative, a cross-institutional collaboration designed in response to the failures of higher education to systematically engage in place. Created to incentivize and resource systemic and cultural shifts across three institutions of higher education in the region, the initiative seeks to increase faculty knowledge and skills in community-based teaching, foster inter- and intracollaborations, expand students’ community-based learning opportunities, and enhance community partnerships. Initial outcomes and stakeholder perceptions are detailed using previous validated research instruments and systemic action research practices. An examination of the three institutions and the seven participating departments reveals how structural and cultural barriers pose heavy challenges to cross-institutional engagement; we also highlight promising countermeasures for effecting change, including inclusive visioning processes and accountability mechanisms. Recommendations aim to support others’ efforts to generate and sustain collaborative engagement.